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850185P

Avanti

08:0 PI(4,5)P2

Avanti Polar Lipids

Synonym(s):

PIP2[4′,5′](8:0/8:0); 110665

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About This Item

Empirical Formula (Hill Notation):
C25H58N3O19P3
CAS Number:
852043-37-9
Molecular Weight:
797.66
UNSPSC Code:
51191904
NACRES:
NA.25

description

1,2-dioctanoyl-sn-glycero-3-phospho-(1′-myo-inositol-4′,5′-bisphosphate) (ammonium salt)

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 100 μg (with stopper and crimp cap (850185P-100ug))
pkg of 1 × 500 μg (with stopper and crimp cap (850185P-500ug))

manufacturer/tradename

Avanti Polar Lipids

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

Inchi Code

1S/C25H49O19P3.3H3N/c1-3-5-7-9-11-13-18(26)39-15-17(41-19(27)14-12-10-8-6-4-2)16-40-47(37,38)44-23-20(28)21(29)24(42-45(31,32)33)25(22(23)30)43-46(34,35)36;;;/h17,20-25,28-30H,3-16H2,1-2H3,(H,37,38)(H2,31,32,33)(H2,34,35,36);3*1H3/t17-,20?,21+,22?,23-,24?,25?;;;/m1.../s1

InChI key

FRWPUPUJRUQWKA-LUIFTQCCSA-N

SMILES string

[H][C@@](COP([O-])(O[C@H]1[C@H](O)[C@@H](OP(O)([O-])=O)[C@H](OP([O-])(O)=O)[C@@H](O)[C@H]1O)=O)(OC(CCCCCCC)=O)COC(CCCCCCC)=O.[NH4+].[NH4+].[NH4+]

General description

Although PI(4,5)P2 is a minor component of cell membranes, it plays a critical role as a substrate for a number of important signaling proteins. PI(4,5)P2 is an intermediate in the IP3/DAG pathway where it is hydrolyzed by phospholipase C to liberate the second messengers, inositol 1,4,5-triphosphate (IP3) and diacylglycerol (DAG). PI(4,5)P2 is also a substrate for PI 3-kinase where it is phosphorylated to PI(3,4,5)P3, an activator of downstream signaling components such as the protein kinase AKT. The dioctanoyl derivative of PI(4,5)P2 is more water soluble than its long chain counterparts.

Application

08:0 PI(4,5)P2 is suitable for use to identify its binding site in transient receptor potential vanilloid 4 (TRPV4 N) terminus. It has been used in in vitro binding assay to determine the binding of G-protein coupled receptor kinases (GRKs) and β2-adrenergic receptor (β2AR).

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (850185P-100ug)
2 mL Amber Serum Vial with Stopper and Crimp Cap (850185P-500ug)

Storage Class Code

11 - Combustible Solids

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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16:0-18:1 PE Avanti Polar Lipids

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Sigma-Aldrich

A5285

Adenosine 5′-diphosphate monopotassium salt dihydrate

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Scott B Hansen et al.
Nature, 477(7365), 495-498 (2011-08-30)
The regulation of ion channel activity by specific lipid molecules is widely recognized as an integral component of electrical signalling in cells. In particular, phosphatidylinositol 4,5-bisphosphate (PIP(2)), a minor yet dynamic phospholipid component of cell membranes, is known to regulate
Structural Basis of TRPV4 N Terminus Interaction with Syndapin/PACSIN1-3 and PIP2
Goretzki B, et al.
Structure, 26(12), 1583-1593 (2018)
George Khelashvili et al.
Biochemistry, 51(39), 7685-7698 (2012-09-07)
Syntaxin (STX) is a N-ethylmaleimide-sensitive factor attachment protein receptor (SNARE) protein that binds to the plasma membrane and regulates ion channels and neurotransmitter transporters. Experiments have established the involvement of the N-terminal segment of STX in direct protein-protein interactions and
Tao Liang et al.
The Journal of biological chemistry, 289(9), 6028-6040 (2014-01-17)
In β-cells, syntaxin (Syn)-1A interacts with SUR1 to inhibit ATP-sensitive potassium channels (KATP channels). PIP2 binds the Kir6.2 subunit to open KATP channels. PIP2 also modifies Syn-1A clustering in plasma membrane (PM) that may alter Syn-1A actions on PM proteins
Structural and functional analysis of a beta2-adrenergic receptor complex with GRK5
Komolov KE, et al.
Cell, 169(3), 407-421 (2017)
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